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32 WBaSO 4
%S = 233 W × 100
compound
32 6.48
... 18.5 = × 100
233 W
W = 4.81 gram
3. Answer (2)
32
%S = × 100 42%
76
4. Answer (2)
O2 + 2C 2CO
5 CO + I2O5 I2 + 5 CO2
5. Answer (1)
Nitrogen is detected by Duma and Kjeldahl method only.
6. Answer (4)
These substances cannot give NH3 gas.
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124 Organic Chemistry Success Achiever (Solutions)
12 WCO2
%C = × 100
44 Wcompound
2 WH2O
%H= × 100
18 Wcompound
62 WMg2P2O7
%P = 222 W × 100
compound
Normality Volume
N
H2SO4 60 mL
5
N
NaOH 20 mL
10
1 60 1 20
(ngeq )NH3
5 1000 10 1000
6 1
(ngeq )NH3
500 500
5 1
(ngeq )NH3
500 100
1
(nmol )N (nmol )NH3 (ngeq )NH3
100
14
(Mass)N 0.14 g
100
0.14
Percentage of "N" 100 = 10%
1.4
141 80
= × × 100 = 24%
188 250
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Success Achiever (Solutions) Organic Chemistry 125
15. Answer (1)
⎡ ⎤
⎢ Mass of Platinichloride 195 – 410 ⎥
⎢ Mass of platinum ⎥
Molar mass of base = ⎢ 2
⎥ × basicity
⎢⎣ ⎥⎦
Molar mass 90
basicity = = =2
Equivalent mass 45
17. Answer (4)
Duma’s method can be used in all nitrogen containing compounds.
18. Answer (1)
It can combine with all Cl, Br, I, P, S, N elements due to high reactivity.
19. Answer (4)
Information based.
20. Answer (4)
All can be converted to vapour state directly from solid state.
21. Answer (1)
Cryoscopic and ebullioscopic methods are for non-volatile solutes.
22. Answer (4)
Fe 2 (SO 4 )
NaOH
FeSO 4 ⎯⎯⎯→ Fe (OH)2 ⎯⎯⎯
NaCN
→ Na 4 ⎡⎢Fe (CN)6 ⎤⎥ ⎯⎯⎯⎯⎯ 3
→ Fe 4 ⎡⎢Fe (CN)6 ⎤⎥
⎣ ⎦ ⎣ ⎦3
green blue
23. Answer (1)
(NH ) MoO
P ⎯⎯
→ Na 3PO 4 ⎯⎯ 4 2
→ H3PO 4 ⎯⎯⎯⎯⎯→
HNO
4
(NH4 )3 PO 4 .12MoO3
3
1 ⎡ mass of Pt salt ⎤
E= ⎢ ×195 − 410⎥
2 ⎢⎣ mass of Pt ⎥⎦
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1 1
2 | 1
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Success Achiever (Solutions) Organic Chemistry 127
40. Answer (2)
It contains 10 electrons.
41. Answer (3)
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128 Organic Chemistry Success Achiever (Solutions)
* O
*
*
*
60. Answer (4)
In hetero cyclic aromatic compounds at least one atom of ring is different.
61. Answer (3)
Initially left ring is less reactive towards nitration due to –R effect but after first nitration on other ring it becomes
more reactive.
62. Answer (3)
After removal of 3rd H, it becomes aromatic
63. Answer (2)
CH3 CH3
| + (CH3 shifting) |
CH3 – C – CH2 CH3 – C – CH2 – CH3
| +
CH3
64. Answer (4)
Fullurenes are allotrope of carbon.
65. Answer (4)
NO2 has strongest electron withdrawing ability.
66. Answer (3)
Due to the presence of vacant d-orbital of appropriate energy in Si atom, it behaves as electron withdrawing
group through mesomerism.
67. Answer (3)
Because charge separated structure is most contributing where negative charge in five-membered ring and
positive charge in seven-membered ring.
68. Answer (2)
In III, aromatic ring is present, hence it has lowest enthalpy of combustion.
69. Answer (2)
70. Answer (2)
(2) is resonance stabilized where delocalization of positive charge is maximum due to resonance.
71. Answer (2)
Planar six-membered ring formation.
72. Answer (1)
Charge separated resonating structure has negligible contribution towards resonance hybrid in option (1).
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Success Achiever (Solutions) Organic Chemistry 129
73. Answer (4)
Structure (4) has maximum number of covalent bonds.
74. Answer (2)
Conjugate base is not stabilized by resonance.
H
O O O O
–H
Unstable
Me Me
> Me > Me Br
Br Br
NBS/h
More stable
Br –H
O
NBS H2O/K2CO3
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130 Organic Chemistry Success Achiever (Solutions)
CO2H
1
H OH
2
H Cl
CH3
At (1),
3 1
4 1 2 3
2 4
It is 'S' configurated.
At (2),
2 1
4 1 3 2
3 4
It is 'R' configurated.
H
CH3
CH3—C*—CH = C
H
C2H5
Two enantiomeric pairs for each cis and trans. So the combination gives 4-diastereomeric pairs.
85. Answer (4)
CH3
CH3
KOH
C2H5—C—Cl HO—C—C2H5
DMF
SN2 H
H
Inversion of
configuration
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Success Achiever (Solutions) Organic Chemistry 131
87. Answer (2)
–
OH
Br
H
Cl (1, 2) axial-equatorial is cis in nature
H
93. Answer (3)
94. Answer (3)
95. Answer (2)
–NH – CH3 is maximum electron donating group among all given groups.
96. Answer (2)
(CH3)3COK is a bulky base and it gives Hoffmann elimination.
97. Answer (3)
Both have 6 valance electrons.
98. Answer (1)
D
CH3 C C2H5
H Chiral centre
Since it has chiral centre therefore it will show optical isomerism.
99. Answer (4)
¨
C2H5
+
MgBr + H O R C2H5 H + R O MgX
Conjugate Conjugate
acid of base of ROH
CH3 CH2
¨
Protonolysis due to proton transfer.
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132 Organic Chemistry Success Achiever (Solutions)
Ether
CH3 Cl +2Na + C2H5 Cl CH3 CH3 + CH2 CH2
CH3 C2H5
C2H5 C2H5
¨O
¨
2CH3COO 2e 2CH3 C
O
CH3 C O CH3 + CO2
(Free radical)
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Success Achiever (Solutions) Organic Chemistry 133
CH3
CH—CH– C
H (A) (B) H CH3
CH3
(A)
CH = CH–CH
CH3
Extension of conjugation
(More stable)
Major product
CH3
(B)
CH2–CH = C
(Minor) CH3
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134 Organic Chemistry Success Achiever (Solutions)
4 1 3
3 2 2 1
Right way Wrong way
of numbering of numbering
116. Answer (1)
OsO4 is used to perform cis-dihydroxylation reaction on alkene.
117. Answer (2)
H3C
C = CH – CH3
H3C
Saytzev's product
Br
Anti-Markonikoff's addition
(Peroxide effect)
O
H3C – C – H
120. Answer (3)
Fact.
121. Answer (2)
Most substituted alkene will have lowest molar heat of hydrogenation.
122. Answer (4)
Oxidation produces diols.
123. Answer (3)
Br
Br2
Br
124. Answer (1)
h
Initiation : R – O – O – R R – O
Propagation :
R – O + H – Br R – OH + Br
125. Answer (4)
Presence of electron withdrawing group in -complex increases potential energy of the system.
126. Answer (4)
Five double bonds, one triple bond and cyclopropyl ring will absorb H2 at higher temperature.
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Success Achiever (Solutions) Organic Chemistry 135
127. Answer (2)
H
CH3 CH CH3 CH2 CH2 B
(Electrophile) H
128. Answer (4)
HgSO4
CH CH CH3 CHO
H2SO4
LiAlH4
CH3 CH2 OH
129. Answer (2)
(i) B2H6 CHO
CH CH
(ii) H2O2/NaOH CHO
The alkynes which has terminal hydrogen always gives aldehyde. While non-terminal alkynes gives ketone.
130. Answer (2)
(i) O3 CHO
CH2 CH CH CH CH CH2 2HCHO + 2
(ii) Zn/H2O CHO
131. Answer (1)
No. of geomaterical isomer is = 2n where n = No. of double bond. When both end are non identical.
O OH ONa
Tautomerism NaNH2
CH3 C CH3 CH3 C CH2 C CH2
CH3
(A)
Addn CH CH
ONa
CH3 C CH3
C CH
(B)
135. Answer (1)
Ether
CH C CH 2Br + Mg CH C CH2MgBr
(A) (B)
Since compound B has acidic (terminal) H, hence it reacts further with (A) and forming propyne
CH C CH2 MgBr + CH C CH2Br CH C CH3 + BrMgC C CH2Br
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As sp3 C is less electronegative than sp3 N alkyl carbanion R is more basic than NH2 . However
Θ
Θ Θ
sp hybridized carbon is more electronegative than sp3 N. Hence NH2 is more basic than HC C
hot Fe
3CH CH Tube
Benzene
142. Answer (3)
Na/C2H5OH CH3 H
CH3 C C CH3 C C
H CH3
D2/Pt
H D
CH3 C C CH3
D H
(Recemic mixture)
143. Answer (1)
(2 carbon 2) hydrogen
Degree of unsaturation =
2
(2 7 2) 12
D.U.
2
D.U. = 2
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Success Achiever (Solutions) Organic Chemistry 137
144. Answer (4)
C2H5
AlCl3/HCl
+ CH2 CH2
368 K
Cl Cl
CH3 H CH3 CH3
+
¨NH ¨ + Cl
–
¨
Benzyne
148. Answer (1)
Due to more prominent +R effect of F .
149. Answer (2)
CH3 CH3
Cl
O3 Zn
O O
+
H
H
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Cl
155. Answer (4)
+
CH2 CH3
+
is more stable, is aromatic
156. Answer (1)
There is no H-atom at anti-position.
157. Answer (3)
Natural polymer is degradable.
158. Answer (4)
SO3 is not primary pollutant.
159. Answer (1)
Exosphere is the uppermost region of atmosphere.
160. Answer (1)
Statosphere.
161. Answer (2)
Fact.
162. Answer (1)
BOD5 means dissolved oxygen consumed in 5 days.
163. Answer (1)
Ozone layer is destroyed by chlorofloro carbon.
164. Answer (1)
Los Angels smog is photochemical smog.
165. Answer (4)
MIC gas released in Bhopal gas tragedy.
166. Answer (4)
Due to very decrease in temperature.
167. Answer (2)
Due to hole in ozone layer, U.V. rays reaches on earth which cause skin cancer.
168. Answer (4)
CO is primary pollutant.
169. Answer (3)
PAN is a secondary pollutant.
170. Answer (2)
Chlorination of water is done to kill germ.
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Success Achiever (Solutions) Organic Chemistry 139
172. Answer (4)
NO2.
173. Answer (1)
N2 is not an air pollutant.
174. Answer (3)
SO3 is not dissociated in smog formation
175. Answer (4)
Seconal is tranquilliger
Et 2O
Br CH2—CH2—CH2—Br + Mg
180. Answer (3)
Covalent character in AgCN due to high polarising power of Ag+ due to its Pseudo noble electronic configuration
so C of CN– is not allowed to attack and hence N of CN– act as nucleophile.
181. Answer (2)
Alkyl fluoride always give alkene that is less substituted which is governed by Hoffman rule.
182. Answer (1)
Function of Red P is to remove I2 as PI3 otherwise I2 react again with C2H6 to form C2H5I.
183. Answer (4)
Stronger base favour elimination while weaker base favour substitution.
The order of basic strength is
R—O– > OH– > C6H5O– > CH3—COO–
184. Answer (4)
Better will be leaving group faster will be rate of reaction.
Leaving group is in order I > Br > Cl > F.
185. Answer (1)
–
CH3—CH CH—COOH + HBr CH3—CH—CH2—COOH
Br
CH3—CH—CH2—COOH
Br
NO2 in a strong electron withdrawing so, CH3 — CH2 — C H— NO 2 is highly unstable.
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CH3
Br *
H –
Br NaI I
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Success Achiever (Solutions) Organic Chemistry 141
191. Answer (2)
Given alkyl halide is 2° and C's are 4° and 2°, so sufficiently hindered, therefore, E2 dominates over
SN2.
Also, polarity of CH3OH (solvent) is not as high as H2O, so E1 is also dominated by E2.
4°
Br
CH3O–
E2
H
(Major product)
(2°)
Br Br
CH3 CH3 Br CH3 Br
SN2
CH—OH + P—Br CH—O—P CH—Br + HO—P
CH3 Br CH3 Br CH3 Br
H
–
Br H
CH3—CH2—C—CH3
O
O=S=O
H O Br
SN2
CH3CH2—C—OH + Cl—S CH3 CH3—CH2—C—CH3
–(OTs–)
CH3 O H
CH3
196. Answer (3)
PCl5
CH3CH2Cl 'B'
Alc. KOH
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HOH
HCCl2—CF3
201. Answer (1)
CH3 O is a strong base and good nucleophile and the substrate is 1° alkyl halide so SN2
202. Answer (4)
More stable will be carbocation, higher will be chance to show SN1 reaction.
CH2 – Cl CH2
III.
OCH3 OCH3
So, II < I < III
Increase stability of carbocation and hence increase reactivity of halides.
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Success Achiever (Solutions) Organic Chemistry 143
207. Answer (3)
More will NO2 group more stable will be intermediate and easy will be aromatic substitution.
208. Answer (4)
All form azodyes.
209. Answer (1)
This is Sand Mayer reaction.
210. Answer (1)
Fact.
211. Answer (3)
CH3
CH3
Cl
CH3
+ – CH3
Na O C CH3
O O O C CH3
CH3
Br CH3
(Product)
The above product does not have any C = C or C C bond, so, it will not give Br2-water test.
Cl
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Cl Cl
Cl
Cl
Cl Cl
Cl2/Fe
Cl Cl
Cl
217. Answer (2)
CH3 CH3
CH3 |
| |
CH—C—CH Re arrangemen t
3 CH — C—CH—CH
CH2 CH—C—CH3 + H2O —— CH3— 3
| |
3
| | |
CH3 OH CH3 OH CH3
(more stable)
ONa OH
OH
COOH
4 – 7 atm
COONa
CO2
H / H2 O
125C
Salicylic acid
O O
O H
–
—C—O
+C O
(E)
Salicylic acid
–
2HNO2—— N O H2 O NO 2
(Electrophi le )
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Success Achiever (Solutions) Organic Chemistry 145
222. Answer (1)
(i) O
CH3 — CH — CH CH — CH3 3
CH3 — CH — CHO CH3 CHO
| (ii)Zn / H2O |
Oxidation
CH3 CH3
– – +1
CH 3—CH CH 2 + OH CH3—CH—CH2 + Cl
|
OH
CH3 — CH— CH2Cl
|
OH
Cl –
623 K OH
300 atm
H Benzyne
OH
(Intermediate)
OH OH
OK
CHO
CHO
343 K
KOH CHCl3
dil HCl
(major)
226. Answer (4)
O
||
The compound which has CH3 — C — or CH3 — CH— group gives iodoform test.
|
OH
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O HI I
Heat
+ I
O OH
+
OH
In Claisen rearrangement, if ortho positions are blocked, allyl group migration para position with same carbon.
CH3 O O
|
Cu
CH3 O3
||
NaNH2
||
CH3 − C − OH ⎯⎯⎯
573K
→ CH2 = C ⎯⎯⎯⎯
Zn−H2O
→ HCHO + CH3 − C − CH3 ⎯⎯⎯⎯
→ CH3 − C− CH2Na
|
CH3 (C) (B)
CH3
First ester (A) will form ketone which will further reacts with grignard reagent and form 3°–Alcohol which reacts
faster with Lucas reagent.
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Success Achiever (Solutions) Organic Chemistry 147
239. Answer (1)
O
|
HCOOC2H5 + CH3MgBr —— H—C—O—C2H5
|
CH3
O OMgBr OH
|| |
|
H / H O
H — C — CH3 C 2H5 OMgBr CH3—C—CH3 2 CH3 — CH— CH3
CH3MgBr
Acetaldehy de | 2 propanol
H
240. Answer (3)
This method is used for the preparation of aldehyde (expect formaldehyde) only.
241. Answer (4)
Fact.
242. Answer (1)
243. Answer (3)
3º allyl radical is formed
244. Answer (3)
OH
is formed
OH
245. Answer (1)
OH OCOONa OH OH
COONa +
COOH
(i) NaOH H
(ii) CO2
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[ Ag(NH3 )2 ]
CH3 – CHO Ag Organic Compound
Silver mirror
O OH
|| |
H
CH3 — C HCN
CH3 — C — CH3
| |
CH3 CN
Cyanohydrine
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Success Achiever (Solutions) Organic Chemistry 149
263. Answer (3)
(A) is carboxylic acid and (B) is anhydride
264. Answer (3)
It is Schimdt reaction
265. Answer (4)
C2H5 C2H5
CH3 CH3
and cannot give HCHO
HI/P
HO COOH
CH3
269. Answer (2)
According to alphabetic order
270. Answer (4)
All can form benzaldehyde
271. Answer (1)
O
CH3 CH3
C CH C CH C
CH3 CH3
272. Answer (3)
– NO2 is EWG and – OCH3 is ERG.
273. Answer (4)
— CHO is deactivating group and –OH and –NH2 have acidic H
274. Answer (3)
Cl OH
I I
H O
CH3 — C — Cl (aq) NaOH CH3 — C — OH 2 CH3 COOH
| | ( Carboxylic acid)
Cl OH
( unstable )
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CH3—CH2—CH—C—OH
Cl
Presence of electron withdrawing group nearest to the carboxylic group increase the acidic strength to
maximum extent.
COONa COOH
633 K HCl
Na CO 2 + NaCl
COONa COOH
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Success Achiever (Solutions) Organic Chemistry 151
290. Answer (1)
CN HCl COOH
| + H2O |
CN COOH
(A) cyanogen
O N—OH NH2
NH2OH LiAlH HNO
4
2
—CH2OH
O O O
|| || || . . H O / H
R — C — Cl + N3H R — C — N3 R — C — N : R—NCO 2 R—NH2
Acylazide
O O
|| CH3 H O/H ||
CH3—CH2— C— N 2 CH3—CH2— C—OH + CH3—NH—C2H5
C 2H 5
299. Answer (4)
P2 O5
COOH
O = C = C = C = O + 2H2O
Carbon suboxide
CH2
COOH CaO/
CH2 = C = O + H2O + CO2
Ketene
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COOH + CH2OH
302. Answer (3)
Amide forms amine. Acetone and acetophenone give haloform test.
303. Answer (2)
O CH2
Fe / H O
2
Out of (CH3)3N, CH3NH2, (CH3)2NH . (CH3)2NH is most basic due to +I effect and hydrogen bonding in H2O.
+I effect
CH3
H3C H
+I effect
O
Hydrogen H H
bonding
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Success Achiever (Solutions) Organic Chemistry 153
308. Answer (1)
Due to maximum resonance stabilised nitrogen atom.
+
NH NH2 NH2
(c)
[Equivalent resonance]
Protonation
KNH NH –
2
2
NH2
Cl
312. Answer (2)
CH3 CH3
| HNO 2
|
CH3 — C — CH2 — NH2
CH3 — C — CH2 — CH3 (followed by rearrangement)
| |
CH3 OH
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NO
|
HNO 2 NaOH
R — CH — R
R — C — R
Blue colour
| |
NO 2 NO 2
NaNO / HCl
HO3S NH2 2 NaO3S N2Cl
N(CH3) 2
NC NH2
H O / H
2 + HCOOH
O–
|
H O2
CH3 — N — CH — CH3 2 CH3 — N — CH — CH3 CH3—CH = CH2 + (CH3)2N—OH
| | | |
CH3 CH3 CH3 CH3
O O O
|| || ||
KOH
S — Cl + R—NH2 S — NH — R S — NK — R
|| || ||
O O O
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Success Achiever (Solutions) Organic Chemistry 155
326. Answer (3)
NaOH
N2Cl
OH O
HO OH
CH2 — OH
N2Cl NH2
+ N N NH2
(yellow dye)
O
CH3
H C N is formed
CH3
N(CH3)2
CH (Malachite)
N(CH3)2
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S.B.
H2N NH2
Benzidine
340. Answer (4)
It is due to polar protic medium.
341. Answer (1)
CH3 − CN ⎯⎯
→ CH3 − COOH + NH3 , CH3 − NC ⎯⎯
→ CH3 − NH2 + HCOOH
HCOOH reduces tollen’s reagent while CH3COOH does not reduce tollen’s reagent.
342. Answer (2)
Diazo salt is an electrophile & Phenoxide is more reactive than phenol towards SE reaction.
343. Answer (2)
344. Answer (4)
345. Answer (4)
R O R O
H2N — C — C — OH + H — NH — C — C — OH
H H
– H2O
R O R
H2N — C — C — NH — C — OH
H H
Peptide linkage
O R O
R
CH — C CH — C
H — HN OH
HN NH
– H2O
HO NH — H
C — CH CH — CH
O R O R
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348. Answer (1)
349. Answer (3)
350. Answer (4)
351. Answer (4)
352. Answer (3)
353. Answer (2)
354. Answer (3)
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nCH2= CH
Peroxide
| |
CN CN n
(PAN)
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NH2
CHO
HI,
(CH–OH)4 CH3–CH2–CH2–CH2–CH2–CH3
n-Hexane
CH2–OH
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Fact.
Fact.
Fact.
Fact.
Fact.
In sucrose carbonyl group glucopyranose and fructo-furanose are used in glycosidic linkage hence loss of
reducing property.
pK a pK b 2.34 4.40
Isoelectric point = 3.37
2 2
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⎡ ⎤
⎢ ⎥
−⎢⎢ NH − CH2 − C − NH − (CH2 ) − C −
⎥
⎥
|| 5 ||
⎢ ⎥
⎢⎣ O O ⎥⎦ n
Nylon-2-Nylon-6
(Step growth polymer)
N
and are aromatic
N N
→ CH2 = CH − C ≡ CH
HC ≡ CH ⎯⎯
↓
CH2 = CH − C = CH2
|
Cl
↓
−⎛ CH2 − CH = C − CH2 −⎟⎟⎞
⎜⎜ |
⎜⎜⎝ ⎟
Cl ⎠⎟n
Neoprene
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424. Answer (2)
The sodium salts of azo dyes containing sulphonic acid (–SO3H) and carboxylic acid (–CO2H) groups are called
acid dyes.
Factual.
The chemicals which are used to bring down the body temperature during high fever are called antipyretics.
Bipropellants consists of two liquids one of which acts as a fuel while other acts as the oxidizer.
Mordant dyes are applied to the fabric after treating them with a metal ion (mordant) which acts as a binding
agent between the dye and the fabric.
OH
COOCH3
Methyl salicylate.
O
||
O–C–CH3
COOH
Aspirin
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Molecular weight 60
n= = =2
Empirical weight 30
58
If 1 g silver is present the weight of organic compound =
42
58 108
If 108 g silver is present the organic compound = = 149.14
42
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451. Answer (3)
Complex is [Fe(H2O)5NO]SO4.
452. Answer (3)
MnS + 2HCl
MnCl2 + H2S
MnCl2 + 2NaOH
Mn(OH)2 + 2NaCl
Br2 + H2O
2HBr + (O)
Mn(OH)2 + O MnO2 + H2O
Black ppt
Al(OH)3 + NaOH
NaAlO 2 + H2O
gelatinous white ppt So luble
NaNO2/HCl
NaOH NaSO3 N=N N(CH3)2
SO3H SO3H
462. Answer (2)
O OH O OH
OH OH
O +
O O
Alizarin
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SO2NH2
Sulphonilamide
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